This is a proposal to investigate the structures and the natures of chemical bonding in complexes formed between alpha-cyclodextrin, its per-methylated derivative, and a series of substituted cinnamic acids and cinnamate anions. These cyclodextrin-cinnamate complexes represent model systems for stereospecific complexations involved in such biological processes as active transport, immune response, and enzyme catalysis. The investigation will focus on the stoichiometries, the complex formation constants, the enthalpies and entropies of complexation, the preferential molecular orientations and the nature of the binding forces in each complex. A selection of diverse experimental techniques will be utilized including spectrophotometry, potentiometry, conductometry, polarimetry, and nmr spectrometry.